Practical Synthesis of N-(Diphenylmethyl)- and N-(1-Adamantyl)amides Directly from Aldehydes via a One-Pot Schmidt and Ritter Reaction Sequence

Abstract

Nonoxidative and noncoupling reaction conditions have been developed for the synthesis of N-(diphenylmethyl)and N-(1-adamantyl)amide derivatives directly from aldehydes by employing the concept of a Schmidt and Ritter reaction sequence in a one-pot operation. The reagent mixture consisting of sodium azide and HBF 4 •OEt 2 in acetic acid converts the aldehydes into their respective nitrile analogues which in situ undergo the Ritter reaction with diphenylmethanol or 1-adamantanol to afford the corresponding N-(diphenylmethyl)or N-(1-adamantyl)amide derivatives in very good yields. The method does not require column chromatographic purification for isolation of the products. With its simple reaction procedure and easy product purification technique, this method outshines earlier conventional twostep methods.

Recent Applications of Ritter Reactions in Organic Syntheses

“…It is important that NaN 3 was converted to a nitrile through Schmidt's reaction, then reacts with 65 to produce the product 66 (Scheme 26). [41] The mechanism of the above‐mentioned reaction was pictured in Scheme 27.…”